CN117384141A - Organic compound, and electronic component and electronic device including the same - Google Patents
Organic compound, and electronic component and electronic device including the same Download PDFInfo
- Publication number
- CN117384141A CN117384141A CN202310073444.7A CN202310073444A CN117384141A CN 117384141 A CN117384141 A CN 117384141A CN 202310073444 A CN202310073444 A CN 202310073444A CN 117384141 A CN117384141 A CN 117384141A
- Authority
- CN
- China
- Prior art keywords
- carbon atoms
- substituted
- unsubstituted
- group
- groups
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000002894 organic compounds Chemical class 0.000 title claims abstract description 35
- 125000004432 carbon atom Chemical group C* 0.000 claims description 108
- 125000003118 aryl group Chemical group 0.000 claims description 75
- 239000010410 layer Substances 0.000 claims description 65
- -1 cyano, methyl Chemical group 0.000 claims description 47
- 125000001424 substituent group Chemical group 0.000 claims description 45
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical class C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 38
- 229910052805 deuterium Inorganic materials 0.000 claims description 34
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 33
- 125000001072 heteroaryl group Chemical group 0.000 claims description 32
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000001624 naphthyl group Chemical group 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 239000004305 biphenyl Substances 0.000 claims description 19
- 235000010290 biphenyl Nutrition 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- 239000011737 fluorine Substances 0.000 claims description 16
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 15
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 14
- 239000002346 layers by function Substances 0.000 claims description 14
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 13
- 125000005561 phenanthryl group Chemical group 0.000 claims description 11
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
- 125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 10
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 10
- 125000000732 arylene group Chemical group 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 7
- 125000001188 haloalkyl group Chemical group 0.000 claims description 7
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004988 dibenzothienyl group Chemical group C1(=CC=CC=2SC3=C(C21)C=CC=C3)* 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000005509 dibenzothiophenyl group Chemical group 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 3
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 claims description 2
- 125000004957 naphthylene group Chemical group 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 37
- 239000000463 material Substances 0.000 description 45
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 30
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 24
- 230000015572 biosynthetic process Effects 0.000 description 18
- 238000003786 synthesis reaction Methods 0.000 description 17
- 239000000243 solution Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 238000002347 injection Methods 0.000 description 14
- 239000007924 injection Substances 0.000 description 14
- 239000002994 raw material Substances 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 230000005525 hole transport Effects 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- 125000005549 heteroarylene group Chemical group 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- 230000000903 blocking effect Effects 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 6
- 229910000027 potassium carbonate Inorganic materials 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000000741 silica gel Substances 0.000 description 6
- 229910002027 silica gel Inorganic materials 0.000 description 6
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 5
- 239000002019 doping agent Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 239000000543 intermediate Substances 0.000 description 5
- 238000001819 mass spectrum Methods 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 4
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 125000002950 monocyclic group Chemical group 0.000 description 4
- 239000003208 petroleum Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- 238000012546 transfer Methods 0.000 description 4
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 3
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 229910052749 magnesium Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 229910052709 silver Inorganic materials 0.000 description 3
- 239000004332 silver Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- XPEIJWZLPWNNOK-UHFFFAOYSA-N (4-phenylphenyl)boronic acid Chemical compound C1=CC(B(O)O)=CC=C1C1=CC=CC=C1 XPEIJWZLPWNNOK-UHFFFAOYSA-N 0.000 description 2
- JWJQEUDGBZMPAX-UHFFFAOYSA-N (9-phenylcarbazol-3-yl)boronic acid Chemical compound C12=CC=CC=C2C2=CC(B(O)O)=CC=C2N1C1=CC=CC=C1 JWJQEUDGBZMPAX-UHFFFAOYSA-N 0.000 description 2
- AMEVJOWOWQPPJQ-UHFFFAOYSA-N 2,4-dichloro-6-phenyl-1,3,5-triazine Chemical compound ClC1=NC(Cl)=NC(C=2C=CC=CC=2)=N1 AMEVJOWOWQPPJQ-UHFFFAOYSA-N 0.000 description 2
- IXHWGNYCZPISET-UHFFFAOYSA-N 2-[4-(dicyanomethylidene)-2,3,5,6-tetrafluorocyclohexa-2,5-dien-1-ylidene]propanedinitrile Chemical compound FC1=C(F)C(=C(C#N)C#N)C(F)=C(F)C1=C(C#N)C#N IXHWGNYCZPISET-UHFFFAOYSA-N 0.000 description 2
- QENGPZGAWFQWCZ-UHFFFAOYSA-N 3-Methylthiophene Chemical compound CC=1C=CSC=1 QENGPZGAWFQWCZ-UHFFFAOYSA-N 0.000 description 2
- LTBWKAYPXIIVPC-UHFFFAOYSA-N 3-bromo-9h-carbazole Chemical compound C1=CC=C2C3=CC(Br)=CC=C3NC2=C1 LTBWKAYPXIIVPC-UHFFFAOYSA-N 0.000 description 2
- ZKGHGKNHPPZALY-UHFFFAOYSA-N 9-(3-bromophenyl)carbazole Chemical compound BrC1=CC=CC(N2C3=CC=CC=C3C3=CC=CC=C32)=C1 ZKGHGKNHPPZALY-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 2
- 230000004888 barrier function Effects 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- GTBOYQQGEZKMBW-UHFFFAOYSA-N boric acid;1,3-diphenylbenzene Chemical compound OB(O)O.C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 GTBOYQQGEZKMBW-UHFFFAOYSA-N 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 239000010406 cathode material Substances 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005684 electric field Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000006872 improvement Effects 0.000 description 2
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 2
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 2
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 description 2
- 238000010791 quenching Methods 0.000 description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 125000001544 thienyl group Chemical group 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- 239000011787 zinc oxide Substances 0.000 description 2
- DLXBGTIGAIESIG-UHFFFAOYSA-N 1,8-dibromonaphthalene Chemical compound C1=CC(Br)=C2C(Br)=CC=CC2=C1 DLXBGTIGAIESIG-UHFFFAOYSA-N 0.000 description 1
- XESMNQMWRSEIET-UHFFFAOYSA-N 2,9-dinaphthalen-2-yl-4,7-diphenyl-1,10-phenanthroline Chemical compound C1=CC=CC=C1C1=CC(C=2C=C3C=CC=CC3=CC=2)=NC2=C1C=CC1=C(C=3C=CC=CC=3)C=C(C=3C=C4C=CC=CC4=CC=3)N=C21 XESMNQMWRSEIET-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- LGLSATMXYQYLKU-UHFFFAOYSA-N 9-(4,6-dichloro-1,3,5-triazin-2-yl)carbazole Chemical compound ClC1=NC(Cl)=NC(N2C3=CC=CC=C3C3=CC=CC=C32)=N1 LGLSATMXYQYLKU-UHFFFAOYSA-N 0.000 description 1
- 229910016036 BaF 2 Inorganic materials 0.000 description 1
- ROFVEXUMMXZLPA-UHFFFAOYSA-N Bipyridyl Chemical group N1=CC=CC=C1C1=CC=CC=N1 ROFVEXUMMXZLPA-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 1
- 229940126062 Compound A Drugs 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910052688 Gadolinium Inorganic materials 0.000 description 1
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 229920001609 Poly(3,4-ethylenedioxythiophene) Polymers 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910001508 alkali metal halide Inorganic materials 0.000 description 1
- 150000008045 alkali metal halides Chemical class 0.000 description 1
- 229910052977 alkali metal sulfide Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical class C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 239000011365 complex material Substances 0.000 description 1
- 229920001940 conductive polymer Polymers 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 150000001975 deuterium Chemical group 0.000 description 1
- 125000004431 deuterium atom Chemical group 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 150000004826 dibenzofurans Chemical class 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000842 isoxazolyl group Chemical group 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 238000000206 photolithography Methods 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical class [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 1
- 239000002356 single layer Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000005649 substituted arylene group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
- C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
The application relates to a cable withOrganic compound, and electronic component and electronic device comprising the same. The structural formula of the organic compound is shown as formula 1, and the organic compound can be applied to an organic electroluminescent device, so that the performance of the device can be remarkably improved.
Description
Technical Field
The application belongs to the technical field of organic materials, and particularly relates to an organic compound, an electronic element comprising the same and an electronic device.
Background
Along with the development of electronic technology and the progress of material science, the application range of electronic components for realizing electroluminescence or photoelectric conversion is becoming wider and wider. Organic electroluminescent devices, such as Organic Light Emitting Diodes (OLEDs), typically include oppositely disposed cathodes and anodes, and a functional layer disposed between the cathodes and anodes. The functional layer is composed of a plurality of organic or inorganic film layers, and generally includes an organic light emitting layer, a hole transporting layer, an electron transporting layer, and the like. When voltage is applied to the cathode and the anode, the two electrodes generate an electric field, electrons at the cathode side move to the organic light-emitting layer under the action of the electric field, holes at the anode side also move to the organic light-emitting layer, the electrons and the holes are combined in the organic light-emitting layer to form excitons, and the excitons are in an excited state to release energy outwards, so that the organic light-emitting layer emits light outwards.
In general, in host material/dopant systems, the choice of host material is critical, as host material has a significant impact on the efficiency and lifetime of the light emitting device. The host material with excellent performance should have suitable molecular weight, higher glass transition temperature and thermal decomposition temperature, high electrochemical stability and good interface contact with the adjacent functional layer material. For a red light host material, the material is required to have good carrier transport capability, have a suitable triplet energy level, and ensure that energy can be effectively transferred from the host material to the guest material in the light emitting process, thereby achieving higher device efficiency.
In the currently reported red light main body material, in order to ensure the carrier mobility of molecules, an aromatic structure containing a large conjugated system is generally selected, so that the T1 energy level of the molecules is low, the injection barrier of the carriers is high, and the exciton recombination efficiency is low; in addition, a single large conjugated aromatic structure also causes defects such as high material evaporation temperature, crystallization and the like, so that an OLED device with long service life is difficult to obtain.
Therefore, providing a light-emitting host material to improve the efficiency and lifetime of the device is a currently urgent problem.
Disclosure of Invention
In view of the foregoing problems of the prior art, it is an object of the present application to provide an organic compound, which can improve the performance of electronic components and electronic devices, and electronic components and electronic devices including the same.
A first aspect of the present application provides an organic compound having a structure represented by formula 1:
wherein Het is 6-18 membered nitrogen-containing heteroarylene;
Ar 1 a substituted or unsubstituted aryl group having 6 to 40 carbon atoms;
Ar 2 selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;
L、L 1 、L 2 and L 3 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;
m is selected from 1 or 2;
L、L 1 、L 2 、L 3 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, haloalkyl group with 1-10 carbon atoms, cycloalkyl group with 3-10 carbon atoms, aryl group with 6-20 carbon atoms or heteroaryl group with 3-20 carbon atoms;
R 1 and R is 2 The two groups are identical or different and are each independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms or substituted or unsubstituted heteroaryl groups with 3 to 20 carbon atoms;
n 1 R represents 1 Number n of (n) 1 Selected from 0, 1, 2When n is 3 or 4 1 When the number is greater than 1, any two R 1 Identical or different, optionally, any two adjacent R 1 Forming an aromatic ring having 6 to 14 carbon atoms;
n 2 r represents 2 Number n of (n) 2 Selected from 0, 1, 2, 3 or 4, when n 2 When the number is greater than 1, any two R 2 Identical or different, optionally, any two adjacent R 2 Forming an aromatic ring having 6 to 14 carbon atoms;
R 1 and R is 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 5 carbon atoms, aryl group having 6 to 12 carbon atoms or heteroaryl group having 3 to 12 carbon atoms.
A second aspect of the present application provides an electronic component comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound.
A third aspect of the present application provides an electronic device comprising the electronic component of the second aspect.
The structure of the organic compound comprises carbazole derivative groups, nitrogen-containing heteroarylene groups and 1, 8-substituted naphthyl groups which are mutually connected through single bonds or arylene groups, the compound formed by directly connecting the nitrogen-containing heteroarylene groups or connecting the nitrogen-containing heteroarylene groups to the 8-position of the naphthyl groups has larger spatial torsion, the glass transition temperature of the material can be improved, the stable amorphous thin film is formed during vapor deposition, and the service life of the device is prolonged. In addition, carbazole and naphthalene are electron-rich groups and can be used as electron donors (D: donor), and nitrogen-containing heteroarylene groups are electron-deficient groups and are suitable to be used as electron accepting groups (A: acceptors), and the three groups are mutually combined to form a D-A-D structure, so that energy transfer of luminescent excitons is facilitated, and the light coupling-out efficiency of an OLED device is improved; in particular, when 1, 8-substituted naphthalene is used as an electron donor, the condensed ring characteristic can lower the T1 energy level of molecules, and the energy transfer efficiency between excitons and a light-emitting guest material is improved. Therefore, the use of the organic compound of the present application as a host material can significantly improve the luminous efficiency and lifetime of the device.
Drawings
The accompanying drawings are included to provide a further understanding of the application and are incorporated in and constitute a part of this specification, illustrate the application and, together with the description, do not limit the application.
Fig. 1 is a schematic structural view of an organic electroluminescent device according to an embodiment of the present application.
Fig. 2 is a schematic diagram of a first electronic device according to an embodiment of the present application.
Reference numerals
100. An anode; 200. a cathode; 300. a functional layer; 310. a hole injection layer; 320. a hole transport layer; 330. an electron blocking layer;
340. an organic light emitting layer; 350. an electron transport layer; 360. an electron injection layer; 400. a first electronic device.
Detailed Description
Exemplary embodiments will now be described more fully with reference to the accompanying drawings. However, the exemplary embodiments may be embodied in many forms and should not be construed as limited to the examples set forth herein; rather, these embodiments are provided so that this disclosure will be thorough and complete, and will fully convey the concept of the exemplary embodiments to those skilled in the art. The described features, structures, or characteristics may be combined in any suitable manner in one or more embodiments. In the following description, numerous specific details are provided to give a thorough understanding of embodiments of the present application.
In a first aspect, the present application provides an organic compound having a structure represented by formula 1:
wherein Het is 6-18 membered nitrogen-containing heteroarylene;
Ar 1 a substituted or unsubstituted aryl group having 6 to 40 carbon atoms;
Ar 2 selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 40 carbon atoms, and substituted or unsubstituted heteroaryl groups with 3 to 40 carbon atoms;
L、L 1 、L 2 and L 3 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;
m is selected from 1 or 2;
L、L 1 、L 2 、L 3 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, haloalkyl group with 1-10 carbon atoms, cycloalkyl group with 3-10 carbon atoms, aryl group with 6-20 carbon atoms or heteroaryl group with 3-20 carbon atoms;
R 1 and R is 2 The two groups are identical or different and are each independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms or substituted or unsubstituted heteroaryl groups with 3 to 20 carbon atoms;
n 1 R represents 1 Number n of (n) 1 Selected from 0, 1, 2, 3 or 4, when n 1 When the number is greater than 1, any two R 1 Identical or different, optionally, any two adjacent R 1 Forming an aromatic ring having 6 to 14 carbon atoms;
n 2 r represents 2 Number n of (n) 2 Selected from 0, 1, 2, 3 or 4, when n 2 When the number is greater than 1, any two R 2 Identical or different, optionally, any two adjacent R 2 Forming an aromatic ring having 6 to 14 carbon atoms;
R 1 and R is 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 5 carbon atoms, aryl group having 6 to 12 carbon atoms or heteroaryl group having 3 to 12 carbon atoms.
In the present application, the organic compound has the structure shown below:
formulas 2-10.
In this application, the terms "optional," "optionally," and "optionally" mean that the subsequently described event or circumstance may, but need not, occur, and that the description includes instances where the event or circumstance occurs or does not. For example, "optionally, any two adjacent substituents x form a ring" means that the two substituents may form a ring but do not necessarily form a ring, including: a scenario in which two adjacent substituents form a ring and a scenario in which two adjacent substituents do not form a ring. As another example, "optionally, any two adjacent R' s 1 The formation of a saturated or unsaturated 3-to 13-membered ring "means any two adjacent R 1 Can be connected with each other to form a saturated or unsaturated 3-13 membered ring, or any two adjacent R 1 Or may exist independently of each other.
In this application, the descriptions "each … … is independently" and "… … is independently" and "… … is independently selected from" may be interchanged, and should be understood in a broad sense, which refers to that specific options expressed between the same symbols in different groups do not affect each other, or that specific options expressed between the same symbols in the same groups do not affect each other. For example, the number of the cells to be processed,wherein each q is independently 0, 1, 2 or 3, and each R "is independently selected from hydrogen, deuterium, fluorine, chlorine", with the meaning: the formula Q-1 represents Q substituent groups R ' on the benzene ring, wherein R ' can be the same or different, and the options of each R ' are not mutually influenced; the formula Q-2 represents that Q atoms are taken from each benzene ring of biphenylThe number q of R 'substituents on two benzene rings of the substituent R' can be the same or different, and each R 'can be the same or different, and the options of each R' are not influenced each other.
In the present application, such terms as "substituted or unsubstituted" mean that the functional group described later in the term may or may not have a substituent (hereinafter, for convenience of description, substituents are collectively referred to as Rc). For example, "substituted or unsubstituted aryl" refers to aryl having a substituent Rc or unsubstituted aryl. Wherein the substituent Rc may be, for example, deuterium, a halogen group, cyano, heteroaryl, aryl, trialkylsilyl, alkyl, haloalkyl, cycloalkyl or the like.
In the present application, the number of carbon atoms of a substituted or unsubstituted functional group refers to all the numbers of carbon atoms. For example, if L is a substituted arylene group having 12 carbon atoms, then the arylene group and all of the substituents thereon have 12 carbon atoms.
Aryl in this application refers to an optional functional group or substituent derived from an aromatic carbocyclic ring. The aryl group may be a monocyclic aryl group (e.g., phenyl) or a polycyclic aryl group, in other words, the aryl group may be a monocyclic aryl group, a condensed ring aryl group, two or more monocyclic aryl groups connected by a carbon-carbon bond conjugate, a monocyclic aryl group and a condensed ring aryl group connected by a carbon-carbon bond conjugate, two or more condensed ring aryl groups connected by a carbon-carbon bond conjugate. That is, two or more aromatic groups conjugated through carbon-carbon bonds may also be considered aryl groups herein unless otherwise indicated. Among them, the condensed ring aryl group may include, for example, a bicyclic condensed aryl group (e.g., naphthyl group), a tricyclic condensed aryl group (e.g., phenanthryl group, fluorenyl group, anthracenyl group), and the like. The aryl group does not contain hetero atoms such as B, N, O, S, P, se, si and the like. For example, in the present application, biphenyl, terphenyl, and the like are aryl groups. Examples of aryl groups may include, but are not limited to, phenyl, naphthyl, fluorenyl, anthryl, phenanthryl, biphenyl, terphenyl, benzo [9,10 ] ]Phenanthryl, pyrenyl, benzofluoranthenyl,A base, etc. In the present application, arylene is referred toA group refers to a divalent group formed by further loss of one hydrogen atom from an aryl group.
In the present application, a substituted aryl group may be one in which one or two or more hydrogen atoms in the aryl group are substituted with a group such as deuterium atom, halogen group, cyano group, aryl group, heteroaryl group, trialkylsilyl group, alkyl group, cycloalkyl group, haloalkyl group, or the like. It is understood that the number of carbon atoms of a substituted aryl refers to the total number of carbon atoms of the aryl and substituents on the aryl, e.g., a substituted aryl having 18 carbon atoms refers to the total number of carbon atoms of the aryl and substituents being 18.
Heteroaryl in this application refers to a monovalent aromatic ring or derivative thereof containing at least one heteroatom in the ring, which may be one or more of B, O, N, P, si, se and S. Heteroaryl groups may be monocyclic heteroaryl or polycyclic heteroaryl, in other words, heteroaryl groups may be a single aromatic ring system or multiple aromatic ring systems that are conjugated through carbon-carbon bonds, with either aromatic ring system being an aromatic monocyclic ring or an aromatic fused ring. Illustratively, heteroaryl groups may include thienyl, furyl, pyrrolyl, imidazolyl, thiazolyl, oxazolyl, oxadiazolyl, triazolyl, pyridyl, bipyridyl, pyrimidinyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phenoxazinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, isoquinolinyl, indolyl, carbazolyl, benzoxazolyl, benzimidazolyl, benzothiazolyl, benzocarbazolyl, benzothienyl, dibenzothiophenyl, thiophenyl, benzofuranyl, phenanthrolinyl, isoxazolyl, thiadiazolyl, phenothiazinyl, silafluorenyl, dibenzofuranyl, and N-phenylcarbazolyl, N-pyridylcarbazolyl, N-methylcarbazolyl, and the like, without limitation thereto. In the present application, the term "heteroarylene" refers to a divalent group formed by further losing one hydrogen atom.
In the present application, a substituted heteroaryl group may be one in which one or more hydrogen atoms in the heteroaryl group are substituted with groups such as deuterium atoms, halogen groups, cyano groups, aryl groups, heteroaryl groups, trialkylsilyl groups, alkyl groups, cycloalkyl groups, haloalkyl groups, and the like. It is understood that the number of carbon atoms of the substituted heteroaryl refers to the total number of carbon atoms of the heteroaryl and substituents on the heteroaryl.
In the present application, as L, L 1 、L 2 、L 3 、Ar 1 And Ar is a group 2 The aryl group of the substituent(s) may have 6 to 20 carbon atoms, for example, may have 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and specific examples of the aryl group as the substituent include, but are not limited to, phenyl, biphenyl, naphthyl, fluorenyl, phenanthryl, anthracenyl,A base.
In the present application, as L, L 1 、L 2 、L 3 、Ar 1 And Ar is a group 2 The heteroaryl group of the substituent(s) may have 3 to 20 carbon atoms, for example, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms, and specific examples of the heteroaryl group as the substituent(s) include, but are not limited to, pyridyl, pyrimidinyl, carbazolyl, dibenzofuranyl, dibenzothienyl, quinolinyl, quinazolinyl, quinoxalinyl, isoquinolinyl.
In the present application, the non-positive connection is referred to as a single bond extending from the ring systemAnd- #, which means that one end of the linkage can be attached to any position in the ring system through which the linkage extends, and the other end is attached to the remainder of the compound molecule.
In the present application, the alkyl group having 1 to 10 carbon atoms may include a straight-chain alkyl group having 1 to 10 carbon atoms and a branched-chain alkyl group having 3 to 10 carbon atoms. The number of carbon atoms of the alkyl group may be, for example, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, and specific examples of the alkyl group include, but are not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, t-butyl, n-pentyl, isopentyl, neopentyl, n-hexyl, n-octyl, 2-ethylhexyl, nonyl, decyl, 3, 7-dimethyloctyl, and the like.
In the present application, the halogen group may be, for example, fluorine, chlorine, bromine, iodine.
Specific examples of trialkylsilyl groups herein include, but are not limited to, trimethylsilyl, triethylsilyl, and the like.
Specific examples of haloalkyl groups herein include, but are not limited to, trifluoromethyl.
In the present application, the cycloalkyl group having 3 to 10 carbon atoms may have 3, 4, 5, 6, 7, 8, or 10 carbon atoms, for example. Specific examples of cycloalkyl groups include, but are not limited to, cyclopentane, cyclohexane, adamantane.
In this application, a ring system formed by n atoms is an n-membered ring. For example, phenyl is a 6 membered aryl. A 6-18 membered nitrogen-containing heteroarylene group refers to a heteroarylene group having 6 to 18 ring atoms, and the ring atoms contain nitrogen atoms.
For example, as shown in the following formula (f), the naphthyl group represented by the formula (f) is linked to other positions of the molecule through two non-positional linkages penetrating through the bicyclic ring, and the meaning of the linkage includes any one of the possible linkages shown in the formulas (f-1) to (f-10).
As another example, as shown in the following formula (X '), the dibenzofuranyl group represented by the formula (X') is linked to the other position of the molecule through an unoositioned linkage extending from the middle of one benzene ring, and the meaning represented by this linkage includes any possible linkage as shown in the formulas (X '-1) to (X' -4).
In the present application, - (L) m -represents m L are connected in sequence.
In some embodiments, het is a 6-14 membered nitrogen containing heteroarylene.
In other embodiments of the present application Het is a 6-membered nitrogen containing heteroarylene, a 10-membered nitrogen containing heteroarylene, a 13-membered nitrogen containing heteroarylene, or a 14-membered nitrogen containing heteroarylene.
In some embodiments, het is selected from the following groups:
- # denotes and L 3 The key to be connected to the key,representing a group with L or L 2 A linked bond; when only one of the Het groups is +.>When (I)>Represents a bond to L, in which case L 2 Is a single bond, ar 2 Is hydrogen, i.e.)>Is not present.
In some more specific embodiments, het is selected from the following groups:
- # denotes and L 3 The key to be connected to the key,representing a group with L or L 2 A linked bond; when only one of the Het groups is +.>When (I)>Represents a bond to L, in which case L 2 Is a single bond, ar 2 Is hydrogen.
In some embodiments, ar 1 Selected from substituted or unsubstituted aryl groups having 6 to 20 carbon atoms. For example, ar 1 A substituted or unsubstituted aryl group selected from the group consisting of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, and 20 carbon atoms.
Preferably Ar 1 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trimethylsilyl, trifluoromethyl, cycloalkyl having 5 to 10 carbon atoms, and aryl having 6 to 12 carbon atoms.
Alternatively, ar 1 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, and substituted or unsubstituted terphenyl.
Preferably Ar 1 Each of the substituents is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl, trifluoromethyl, cyclopentane, cyclohexane, adamantane, phenyl, naphthyl, or biphenyl.
Alternatively, ar 1 Selected from a substituted or unsubstituted group W, wherein the unsubstituted group W is selected from the following groups:
wherein the substituted group W has one or more substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl, trifluoromethyl, cyclopentane, cyclohexane, adamantane, phenyl, naphthyl or biphenyl, and when the number of substituents is greater than 1, the substituents are the same or different.
Alternatively, ar 1 Selected from the following groups:
in some embodiments, ar 1 Selected from the following groups:
in some embodiments, ar 2 Selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups having 5 to 18 carbon atoms. For example, ar 2 A substituted or unsubstituted aryl group selected from the group consisting of 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25 and a substituted or unsubstituted heteroaryl group having 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18 carbon atoms.
Preferably Ar 2 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trimethylsilyl, trifluoromethyl, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, and heteroaryl having 5 to 12 carbon atoms.
Alternatively, ar 2 Selected from the group consisting of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl.
Preferably Ar 2 Each of the substituents is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl, trifluoromethyl, cyclopentane, cyclohexane, adamantane, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl.
Alternatively, ar 2 Selected from hydrogen or a substituted or unsubstituted group V, wherein the unsubstituted group V is selected from the following groups:
wherein the substituted group V has one or more substituents independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, trimethylsilyl, trifluoromethyl, cyclopentane, cyclohexane, adamantane, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl, and when the number of the substituents is greater than 1, the substituents are the same or different.
Alternatively, ar 2 Selected from hydrogen or the following groups:
in some embodiments, ar 2 Selected from hydrogen or the following groups:
in some embodiments, L, L 1 、L 2 And L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms. For example L, L 1 、L 2 And L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20 carbon atoms.
Preferably L, L 1 、L 2 And L 3 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, or aryl having 6 to 12 carbon atoms.
Optionally L, L 1 、L 2 And L 3 Each independently selected from a single bond, a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted biphenylene group.
Preferably L, L 1 、L 2 And L 3 Each of the substituents in (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl or biphenyl.
Alternatively, L 1 、L 2 And L 3 Each independently selected from a single bond or the following groups:
further alternatively, L 1 、L 2 And L 3 Each independently selected from a single bond or the following groups:
alternatively, - (L) m -a single bond or a group selected from:
further optionally, - (L) m -a single bond or a group selected from:
in one embodiment of the present application, R 1 And R is 2 Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, substituted or unsubstituted carbazolyl; or any two adjacent R 1 Forming benzene ring and naphthalene ring; or any two adjacent R 2 Forming benzene ring and naphthalene ring.
Preferably, R 1 And R is 2 Each of the substituents is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothienyl or carbazolyl.
Alternatively, R 1 And R is 2 Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl, deuterium substituted phenyl, naphthyl, biphenyl, phenanthryl, pyridyl, quinolinyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, N-carbazolyl, or N-phenylcarbazolyl; or any two adjacent R 1 Forming benzene ring and naphthalene ring; or any two adjacent R 2 Forming benzene ring and naphthalene ring.
Alternatively, R 1 And R is 2 Each independently selected from deuterium, fluorine, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl or the following groups:
further alternatively, R 1 And R is 2 Each independently selected from deuterium, fluorine, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl or the following groups:
optionally, the organic compound is selected from the group consisting of:
/>
/>
/>
/>
/>
/>
/>
in a second aspect, the present application provides an electronic component comprising an anode and a cathode disposed opposite each other, and a functional layer disposed between the anode and the cathode; the functional layer comprises the organic compound of the present application.
Optionally, the functional layer comprises an organic light emitting layer comprising an organic compound as described herein.
Optionally, the electronic element is an organic electroluminescent device or a photoelectric conversion device.
In one embodiment, the electronic component is an organic electroluminescent device. As shown in fig. 1, the organic electroluminescent device may include an anode 100, a hole transport layer 320, an electron blocking layer 330, an organic light emitting layer 340, an electron transport layer 350, and a cathode 200, which are sequentially stacked.
In a specific embodiment, the organic electroluminescent device is a red organic electroluminescent device.
Alternatively, the anode 100 includes an anode material that is optionally a material with a large work function that facilitates hole injection into the functional layer. Specific examples of the anode material include: metals such as nickel, platinum, vanadium, chromium, copper, zinc and gold or alloys thereof; metal oxides such as zinc oxide, indium Tin Oxide (ITO), and Indium Zinc Oxide (IZO); combined metal and oxide such as ZnO: al or SnO 2 Sb; or conductive polymers such as poly (3-methylthiophene) and poly [3,4- (ethylene-1, 2-dioxy) thiophene](PEDT), polypyrrole, and polyaniline, but not limited thereto. Preferably, a transparent electrode including Indium Tin Oxide (ITO) as an anode is included.
Alternatively, hole transport layer 320 comprises one or more hole transport materials, which may be selected from carbazole multimers, carbazole-linked triarylamine compounds, or other types of compounds, as may be selected by those skilled in the art with reference to the prior art. For example, the hole transport layer is made of a material selected from the group consisting of:
/>
In one embodiment, hole transport layer 320 is HT-1.
Optionally, electron blocking layer 330 includes one or more electron blocking materials, which may be selected from carbazole polymers or other types of compounds, as not particularly limited in this application. In one embodiment, the electron blocking layer 330 is TCAC.
Alternatively, the organic light emitting layer 340 may be composed of a single light emitting layer material, and may also include a host material and a dopant material. Alternatively, the organic light emitting layer 340 is composed of a host material and a dopant material, and holes injected into the organic light emitting layer 340 and electrons injected into the organic light emitting layer 340 may be recombined at the organic light emitting layer 340 to form excitons, which transfer energy to the host material, which transfers energy to the dopant material, thereby enabling the dopant material to emit light.
The host material of the organic light emitting layer 340 may be a metal chelate compound, a bisstyryl derivative, an aromatic amine derivative, a dibenzofuran derivative, or other types of materials, which are not particularly limited in this application. The host material may be a single host material or a mixed host material.
In one embodiment of the present application, the host material of the organic light emitting layer 340 is an organic compound of the present application.
The doping material of the organic light emitting layer 340 may be selected with reference to the related art, and may be selected from iridium (III) organometallic complexes, platinum (II) organometallic complexes, ruthenium (II) complexes, and the like, for example. Specific examples of doped materials include but are not limited to,
Eu(dbm) 3 (Phen)Ir(flq) 2 (acac)。
in one embodiment of the present application, the doping material of the organic light emitting layer 340 is Ir (flq) 2 (acac)。
Alternatively, the electron transport layer 350 may be a single layer structure or a multi-layer structure, and may include one or more electron transport materials, which may generally include a metal complex or/and a nitrogen-containing heterocyclic derivative, where the metal complex material may be selected from, for example, liQ, alq 3 、Bepq 2 Etc.; the nitrogen-containing heterocyclic derivative may be an aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, a condensed aromatic ring having a nitrogen-containing six-membered ring or five-membered ring skeleton, or the like, and specific examples include, but are not limited to, 1, 10-phenanthroline-based compounds such as ET-01, bphen, NBphen, DBimiBphen, bimiBphen, or the like, or heteroaryl-containing groups having the structures shown belowAnthracene compounds, triazines or pyrimidines. In one embodiment of the present application, electron transport layer 350 is comprised of ET-01 and LiQ.
In this application, the cathode 200 may include a cathode material, which is a material having a small work function that contributes to electron injection material into the functional layer. Specific examples of the cathode material include, but are not limited to, metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; or a multi-layer material such as LiF/Al, liq/Al, liO 2 Al, liF/Ca, liF/Al and BaF 2 and/Ca. A metal electrode containing magnesium and silver is preferably included as a cathode.
Optionally, as shown in fig. 1, a hole injection layer 310 may be further provided between the anode 100 and the hole transport layer 320 to enhance the ability to inject holes into the hole transport layer 320. The hole injection layer 310 may be a benzidine derivative, a starburst arylamine compound, a phthalocyanine derivative, or other materials, which are not particularly limited in this application. For example, the hole injection layer 310 contains a compound selected from the group consisting of:
in one embodiment of the present application, hole injection layer 310 is F4-TCNQ.
Optionally, as shown in fig. 1, an electron injection layer 360 is further provided between the cathode 200 and the electron transport layer 350 to enhance the ability to inject electrons into the electron transport layer 350. The electron injection layer 360 may include an inorganic material such as an alkali metal sulfide, an alkali metal halide, or may include a complex of an alkali metal and an organic substance. In one embodiment of the present application, electron injection layer 360 is LiQ.
A third aspect of the present application provides an electronic device comprising the electronic component provided in the second aspect of the present application.
According to one embodiment, as shown in fig. 2, the electronic device is a first electronic device 400, and the first electronic device 400 includes the organic electroluminescent device described above. The first electronic device 400 may be, for example, a display device, a lighting device, an optical communication device, or other types of electronic devices, and may include, for example, but not limited to, a computer screen, a mobile phone screen, a television, an electronic paper, an emergency lighting device, an optical module, etc.
The synthesis method of the organic compound of the present application is specifically described below in connection with synthesis examples, but the present application is not limited thereto.
All compounds of the synthetic methods not mentioned in the present application are commercially available starting products.
Synthesis example
1. Synthesis of IM Cz-x
Synthesis of IM Cz-01:
to the reaction flask were charged 3-bromocarbazole (10.00 g,40.63 mmol), 9-phenylcarbazole-3-boronic acid (12.25 g,42.66 mmol), tetrakis (triphenylphosphine) palladium (0.94 g,0.81 mmol), tetrabutylammonium bromide (2.62 g,8.13 mmol), potassium carbonate (12.35 g,89.39 mmol), toluene (100 mL), ethanol (40 mL) and water (20 mL), and the mixture was heated to reflux under nitrogen protection and stirred for 5 hours. After the reaction solution was cooled to room temperature, the reaction solution was extracted with methylene chloride and water, the organic layer was dried over anhydrous magnesium sulfate and filtered, and after filtration, the filtrate was passed through a short silica gel column, the solvent was distilled off under reduced pressure, and the crude product was purified by recrystallization using methylene chloride/petroleum ether (1:4) to give IM Cz-01 (13.03 g, yield 78.5%).
IM Cz-x was synthesized in the same manner as IM Cz-01 except that starting material 1 was used in place of 3-bromocarbazole and starting material 2 was used in place of 9-phenylcarbazole-3-boronic acid, with the main starting materials used, the synthesized intermediates and their yields shown in Table 1.
TABLE 1
2. Synthesis of IM BN-x
Synthesis of IM BN-1
1, 8-dibromonaphthalene (10.00 g,34.97 mmol), 4-biphenylboronic acid (6.93 g,34.97 mmol), tetrakis (triphenylphosphine) palladium (0.81 g,0.70 mmol), tetrabutylammonium bromide (2.25 g,6.99 mmol), potassium carbonate (10.63 g,76.93 mmol), toluene (100 mL), ethanol (40 mL) and water (20 mL) were charged into the reaction flask, and the mixture was heated to reflux under nitrogen and stirred for 5 hours. After the reaction solution was cooled to room temperature, the reaction solution was extracted with dichloromethane and water, and the organic layer was dried over anhydrous magnesium sulfate and filtered; after filtration, the filtrate was passed through a short silica gel column, and the solvent was distilled off under reduced pressure, and the obtained crude product was purified by silica gel column chromatography using ethyl acetate/n-heptane (1:5) as a mobile phase, and the solvent was distilled off under reduced pressure by passing through the column liquid to obtain IM BN-1 (7.65 g, yield 60.9%).
IM BN-x was synthesized in the same manner as IM BN-1 except that raw material 3 was used in place of 4-biphenylboronic acid, the main raw materials used, the synthesized intermediates and their yields are shown in Table 2.
TABLE 2
3. Synthesis of IM Nx
Synthesis of IM N1
Into the reaction flask were charged IM BN-1 (4.00 g,11.13 mmol), m-xylylene diboronic acid (2.20 g,11.13 mmol), tetrakis (triphenylphosphine) palladium (0.26 g,0.22 mmol), tetrabutylammonium bromide (0.72 g,2.23 mmol), potassium carbonate (3.38 g,24.49 mmol), toluene (40 mL), ethanol (10 mL) and water (5 mL), and the mixture was heated to reflux under nitrogen and stirred for 5 hours. After the reaction solution was cooled to room temperature, the reaction solution was extracted with methylene chloride and water, the organic layer was dried over anhydrous magnesium sulfate and filtered, the filtrate was filtered through a short silica gel column, the solvent was removed by distillation under reduced pressure, and the obtained crude product was purified by silica gel column chromatography using ethyl acetate/N-heptane (1:5) as a mobile phase, and the solvent was removed by distillation under reduced pressure through the column to give IM N1 (2.87 g, yield 64.5%).
IM Nx was synthesized in the same manner as IM N1, except that raw material 4 was used instead of isophthalic acid, respectively, wherein the main raw materials used, the synthesized intermediates, and the yields thereof are shown in table 3.
TABLE 3 Table 3
/>
4. Synthesis of IM Tr-Cz-x
Synthesis of IM Tr-Cz-01
To the reaction flask were charged 8-phenyl-1-naphthalene boronic acid (4.80 g,19.35 mmol), 9- (4, 6-dichloro- [1,3,5] triazin-2-yl) -carbazole (6.09 g,19.34 mmol), palladium acetate (0.22 g,0.97 mmol), 2-dicyclohexylphosphine-2, 4, 6-triisopropylbiphenyl (0.46 g,0.97 mmol), potassium carbonate (5.88 g,42.56 mmol), toluene (50 mL), ethanol (20 mL) and water (10 mL), and the mixture was heated to reflux under nitrogen atmosphere and stirred for 5 hours. After the reaction solution was cooled to room temperature, the reaction solution was extracted with methylene chloride and water, the organic layer was dried over anhydrous magnesium sulfate and filtered, and after filtration, the filtrate was filtered through a short silica gel column, and the solvent was distilled off under reduced pressure, and the crude product was recrystallized using an ethyl acetate/petroleum ether (1:3) system to give IM Tr-Cz-01 (6.75 g, yield 72.2%).
The same procedure as for IM Tr-Cz-01 was used to synthesize IM-Tr-Cz-x shown in Table 4, except that IM Nx was used in place of 8-phenyl-1-naphthalene boric acid, and the intermediate synthesized from the main raw material used and the yield thereof were as shown in Table 4.
TABLE 4 Table 4
5. Synthesis of IM Tr-x
Synthesis of IM Tr-01
To the reaction flask were charged 8-phenyl-1-naphthalene boric acid (5.50 g,22.17 mmol), 2, 4-dichloro-6-phenyl-1, 3, 5-triazine (5.01 g,22.17 mmol), palladium acetate (0.25 g,1.11 mmol), 2-dicyclohexylphosphine-2, 4, 6-triisopropylbiphenyl (0.53 g,1.11 mmol), potassium carbonate (6.74 g,48.77 mmol) and toluene (55 mL), ethanol (20 mL) and water (10 mL), and the mixture was heated to reflux under nitrogen and stirred for 4 hours. After the reaction solution was cooled to room temperature, the reaction solution was extracted with methylene chloride and water, the organic layer was dried over anhydrous magnesium sulfate and filtered, and after filtration, the filtrate was filtered through a short silica gel column, the solvent was distilled off under reduced pressure, and the crude product was recrystallized using ethyl acetate/petroleum ether (1:3) to give IM Tr-01 (6.32 g, yield 72.4%).
The same procedure as for IM Tr-01 was used to synthesize IM Tr-x shown in Table 5, except that IM Nx was used instead of 8-phenyl-1-naphthalene boric acid and raw material 5 was used instead of 2, 4-dichloro-6-phenyl-1, 3, 5-triazine, wherein the main raw materials, synthesized intermediates and the yields thereof were as shown in Table 5.
TABLE 5
/>
/>
6. Synthesis of Compounds
(1) Synthesis of compound a 04:
into the reaction flask were charged IM Tr-Cz-01 (6.00 g,12.42 mmol), (3, 5-diphenylbenzene) boric acid (3.58 g,13.05 mmol), palladium acetate (0.14 g,0.62 mmol), 2-dicyclohexylphosphine-2, 4, 6-triisopropylbiphenyl (0.29 g,0.62 mmol), potassium carbonate (3.78 g,27.33 mmol), toluene (60 mL), ethanol (25 mL) and water (15 mL), and the mixture was heated to reflux under nitrogen atmosphere and stirred for 5 hours. After the reaction solution was cooled to room temperature, the reaction solution was extracted with dichloromethane and water, the organic layer was dried over anhydrous magnesium sulfate and filtered, the filtrate was filtered through a short silica gel column, the solvent was removed by distillation under reduced pressure, and the crude product was recrystallized using toluene/n-heptane (1:3) system to give compound a04 (4.92 g, yield 58.5%), mass spectrum (m/z) =677.3 [ m+h] + 。
The compounds shown in Table 6 were synthesized in the same manner as in the compound A04 except that IM-Tr-Cz-x was used in place of IM Tr-Cz-01, and raw material 6 was used in place of (3, 5-diphenylbenzene) boric acid, wherein the main raw materials used, the synthesized compounds and the yield spectra thereof were as shown in Table 6.
(2) Synthesis of compound a 07:
at N 2 IM Tr-01 (5.06 g,12.85 mmol), IM Cz-01 (5.00 g,12.24 mmol), sodium hydride (0.44 g,18.36 mmol) and dry DMF (50 mL) were added sequentially to the three-neck flask under protection, and stirred at room temperature for 6h; adding 50mL deionized water to quench the reaction, extracting the reaction solution with toluene, washing with water to neutrality, separating, drying, filtering, concentrating the filtrate under reduced pressure to obtain solid, stopping distillation, naturally standing, cooling to room temperature, recrystallizing the precipitated crystal with toluene/n-hexane, and oven drying to obtain compound A07 (4.93 g, yield 52.6%), and mass spectrum (m/z) =766.3 [ M+H ] ] + 。
The compounds in Table 7 were prepared in the same synthesis as the compound A07 except that IM Tr-x was used in place of IM Tr-01 and raw material 7 was used in place of IM Cz-01, wherein the main raw materials used, the synthesized compounds and their yields and mass spectra are shown in Table 7.
TABLE 7
/>
(3) Synthesis of Compound A134:
at N 2 Under the protection, adding 9- (3-bromophenyl) -9H-carbazole into the three-neck flask3.20g,9.93 mmol) and dry THF (35 mL), after stirring and dissolving uniformly, cooling to-78 ℃ by using a liquid nitrogen/ethanol bath, then slowly dropwise adding n-butyllithium hexane solution (6 mL,12.00 mmol) with the concentration of 2M, keeping the temperature and stirring for 1h after the dropwise adding, then adding IM Tr-11 (5.16 g,9.93 mmol), keeping the temperature and stirring for 30min, then slowly heating to room temperature, adding dilute hydrochloric acid to quench the reaction, and adjusting the pH to 5-6. Extracting the reaction solution with dichloromethane, washing the organic phase with water to neutrality, separating, drying, filtering, evaporating under reduced pressure to remove solvent, recrystallizing the crude product with toluene/petroleum ether to obtain white crystal A134 (3.90 g, yield 54.0%), and subjecting mass spectrum (m/z) =727.3 [ M+H ]] + 。
The compounds shown in Table 8 were synthesized in the same manner as in the compound A134 except that IM Tr-x was used in place of IM Tr-11 and raw material 8 was used in place of 9- (3-bromophenyl) -9H-carbazole, wherein the main raw materials used, the synthesized compounds and their yields and mass spectra are shown in Table 8.
TABLE 8
/>
The nuclear magnetic data of some compounds are shown below:
nuclear magnetic data of compound a 07: 1 H-NMR(CDCl 3 ,300MHz):δ(ppm)8.68(d,1H),8.57-8.53(m,2H),8.35(s,1H),8.24(d,1H),8.20(d,1H),8.13(s,1H),8.10-8.07(m,2H),7.98(d,1H),7.95(d,1H),7.83-7.75(m,4H),7.64-7.53(m,9H),7.51-7.47(m,4H),7.44(t,1H),7.37-7.31(m,3H),7.26-7.22(m,2H),7.13(d,1H).
nuclear magnetic data of compound a 22: 1 H-NMR(CDCl 3 ,300MHz):δ(ppm)8.85(s,1H),8.59(d,1H),8.35-8.27(m,2H),8.20(d,2H),8.12(d,2H),7.88-7.84(m,3H),7.75(d,2H),7.72-7.66(m,6H),7.59(d,2H),
7.55-7.47(m,8H),7.42(t,1H),7.27-7.23(m,3H),7.19(d,1H).
nuclear magnetic data of compound a 134: 1 H-NMR(CDCl 3 ,300MHz):δ(ppm)8.87(d,2H),8.72(d,1H),8.51(s,1H),8.45(d,1H),8.40(d,1H),8.33-8.29(m,1H),8.06(d,2H),7.87-7.71(m,5H),7.68-7.62(m,5H),7.59-7.54(m,4H),7.47-7.41(m,5H),7.34(t,2H),7.25(t,2H),7.19-7.14(m,2H).
nuclear magnetic data of compound B122: 1 H-NMR(CDCl 3 delta (ppm) 8.91 (d, 1H), 8.68 (s, 1H), 8.37 (s, 1H), 8.23-8.15 (m, 4H), 8.09 (d, 1H), 8.02-7.09 (m, 2H), 7.87 (d, 1H), 7.81-7.78 (m, 3H), 7.74-7.68 (m, 4H), 7.65-7.54 (m, 6H), 7.52-7.49 (m, 2H), 7.46-7.39 (m, 5H), 7.36-7.33 (m, 1H), 7.26-7.21 (m, 2H), 7.13 (d, 1H). Organic electroluminescent device preparation and evaluation:
example 1: preparation of red organic electroluminescent device
Will be of the thickness ofThe ITO/Ag/ITO substrate (manufactured by Corning) was cut into a size of 40mm (length). Times.40 mm (width). Times.0.7 mm (thickness), and a test substrate having an anode and an insulating layer pattern was prepared by a photolithography step using ultraviolet ozone and O 2 ∶N 2 And the plasma is used for surface treatment to improve the work function of the anode of the substrate.
First, F4-TCNQ was vacuum-deposited on an experimental substrate (anode) to a thickness ofIs deposited with HT-1 on the hole injection layer to form a layer with a thickness of +.>Is provided.
Vacuum evaporating TCAC on the hole transport layer to form a film with a thickness ofIs a barrier to electrons.
On the electron blocking layer, compound A04 and Compound Ir (flq) 2 (acac) in a vapor deposition ratio of 98.5% to 1.5%Vapor deposition is carried out simultaneously to form the film with the thickness ofIs provided.
Co-evaporating the compound ET-01 and LiQ on the organic light-emitting layer at an evaporation ratio of 1:1 to form a film having a thicknessIs deposited on the electron transport layer to form a layer with a thickness of +.>Then vacuum evaporating magnesium (Mg) and silver (Ag) on the electron injection layer at an evaporation rate of 1:9 to form a film having a thickness +.>Is provided.
Finally, the CP-01 is evaporated on the cathode to form the cathode with the thickness ofThereby completing the fabrication of the red organic light emitting device.
Examples 2 to 31
An organic electroluminescent device was fabricated by the same method as in example 1, except that the compound a04 was replaced with the compound shown in table 10 as a host material of the light emitting layer at the time of forming the organic light emitting layer.
Comparative examples 1 to 5
An organic electroluminescent device was fabricated in the same manner as in example 1, except that compound A, B, C, D, E was used instead of compound a04 as a host material for the light-emitting layer when the organic light-emitting layer was formed.
The main material structures used in the above examples and comparative examples are shown in table 9 below.
TABLE 9
The devices prepared in examples and comparative examples were tested for performance, wherein IVL (drive voltage, current efficiency, color coordinates) data were at 15mA/cm 2 Tested at current density, T95 lifetime was 30mA/cm 2 The results of the test at current density are shown in Table 10.
Table 10
/>
As can be seen from the results of Table 10, examples 1 to 31 using the organic compound of the present application as an organic light-emitting layer have an improvement in current efficiency (Cd/A) of at least 13.04% and an improvement in lifetime of at least 11% as compared with the device comparative examples 1 to 5 corresponding to the known compound.
The preferred embodiments of the present application have been described in detail above, but the present application is not limited to the specific details of the above embodiments, and various simple modifications may be made to the technical solutions of the present application within the scope of the technical concept of the present application, and all the simple modifications belong to the protection scope of the present application.
Claims (16)
1. An organic compound, characterized in that the organic compound has a structure represented by formula 1:
wherein Het is 6-18 membered nitrogen-containing heteroarylene;
Ar 1 a substituted or unsubstituted aryl group having 6 to 40 carbon atoms;
Ar 2 selected from hydrogen, substituted or unsubstituted aryl groups having 6 to 40 carbon atoms, and carbon atomsSubstituted or unsubstituted heteroaryl having 3 to 40 atoms;
L、L 1 、L 2 and L 3 The same or different and are each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 30 carbon atoms;
m is selected from 1 or 2;
L、L 1 、L 2 、L 3 、Ar 1 and Ar is a group 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group with 1-10 carbon atoms, trialkylsilyl group with 3-12 carbon atoms, haloalkyl group with 1-10 carbon atoms, cycloalkyl group with 3-10 carbon atoms, aryl group with 6-20 carbon atoms or heteroaryl group with 3-20 carbon atoms;
R 1 and R is 2 The two groups are identical or different and are each independently selected from deuterium, halogen groups, cyano groups, alkyl groups with 1 to 10 carbon atoms, trialkylsilyl groups with 3 to 12 carbon atoms, cycloalkyl groups with 3 to 10 carbon atoms, substituted or unsubstituted aryl groups with 6 to 20 carbon atoms or substituted or unsubstituted heteroaryl groups with 3 to 20 carbon atoms;
n 1 r represents 1 Number n of (n) 1 Selected from 0, 1, 2, 3 or 4, when n 1 When the number is greater than 1, any two R 1 Identical or different, optionally, any two adjacent R 1 Forming an aromatic ring having 6 to 14 carbon atoms;
n 2 r represents 2 Number n of (n) 2 Selected from 0, 1, 2, 3 or 4, when n 2 When the number is greater than 1, any two R 2 Identical or different, optionally, any two adjacent R 2 Forming an aromatic ring having 6 to 14 carbon atoms;
R 1 and R is 2 The substituents in (a) are the same or different and are each independently selected from deuterium, halogen group, cyano group, alkyl group having 1 to 5 carbon atoms, aryl group having 6 to 12 carbon atoms or heteroaryl group having 3 to 12 carbon atoms.
2. An organic compound according to claim 1, wherein Het is selected from the following groups:
- # denotes and L 3 The key to be connected to the key,representing a group with L or L 2 A linked bond; when only one of the Het groups is +.>When (I)>Represents a bond to L, in which case L 2 Is a single bond, ar 2 Is hydrogen.
3. The organic compound according to claim 1, wherein Ar 1 A substituted or unsubstituted aryl group having 6 to 20 carbon atoms;
preferably Ar 1 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trimethylsilyl, trifluoromethyl, cycloalkyl having 5 to 10 carbon atoms, and aryl having 6 to 12 carbon atoms.
4. The organic compound according to claim 1, wherein Ar 1 Selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, and substituted or unsubstituted terphenyl;
preferably Ar 1 Each of the substituents is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl, trifluoromethyl, cyclopentane, cyclohexane, adamantane, phenyl, naphthyl, or biphenyl.
5. The organic compound according to claim 1, wherein Ar 1 Selected from the following groups:
6. the organic compound according to claim 1, wherein Ar 2 Selected from hydrogen, substituted or unsubstituted aryl groups with 6 to 25 carbon atoms, and substituted or unsubstituted heteroaryl groups with 5 to 18 carbon atoms;
preferably Ar 2 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, trimethylsilyl, trifluoromethyl, cycloalkyl having 5 to 10 carbon atoms, aryl having 6 to 12 carbon atoms, and heteroaryl having 5 to 12 carbon atoms.
7. The organic compound according to claim 1, wherein Ar 2 Selected from the group consisting of hydrogen, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted biphenyl, substituted or unsubstituted fluorenyl, substituted or unsubstituted phenanthryl, substituted or unsubstituted terphenyl, substituted or unsubstituted pyridyl, substituted or unsubstituted quinolinyl, substituted or unsubstituted dibenzofuranyl, substituted or unsubstituted dibenzothienyl, and substituted or unsubstituted carbazolyl;
preferably Ar 2 Each of the substituents is independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl, trifluoromethyl, cyclopentane, cyclohexane, adamantane, phenyl, naphthyl, biphenyl, dibenzofuranyl, dibenzothiophenyl, or carbazolyl.
8. The organic compound according to claim 1, wherein Ar 2 Selected from hydrogen or the following groups:
9. the organic compound according to claim 1, wherein L, L 1 、L 2 And L 3 Each independently selected from a single bond, a substituted or unsubstituted arylene group having 6 to 20 carbon atoms;
preferably L, L 1 、L 2 And L 3 The substituents in (a) are each independently selected from deuterium, fluorine, cyano, alkyl having 1 to 5 carbon atoms, or aryl having 6 to 12 carbon atoms.
10. The organic compound according to claim 1, wherein L, L 1 、L 2 And L 3 Each independently selected from a single bond, a substituted or unsubstituted phenylene, a substituted or unsubstituted naphthylene, a substituted or unsubstituted biphenylene;
preferably L, L 1 、L 2 And L 3 Each of the substituents in (a) is independently selected from deuterium, fluorine, cyano, methyl, ethyl, isopropyl, tert-butyl, phenyl, naphthyl or biphenyl.
11. The organic compound according to claim 1, wherein L 1 、L 2 And L 3 Each independently selected from a single bond or the following groups:
alternatively, - (L) m -a single bond or a group selected from:
12. the organic compound according to claim 1, wherein R 1 And R is 2 Each independently selected from deuterium, fluoro, cyano, methyl, ethyl, isopropyl, t-butyl, trimethylsilyl, deuterium substituted phenyl, naphthyl, biphenyl, phenanthryl, pyridyl, quinolinyl, 9-dimethylfluorenyl, dibenzofuranyl, dibenzothiophenyl, N-carbazolyl, or N-phenylcarbazolyl; or any two adjacent R 1 Forming benzene ring and naphthalene ring; or any two adjacent R 2 Forming benzene ring and naphthalene ring.
13. The organic compound according to claim 1, wherein the organic compound is selected from the group consisting of:
/>
14. an electronic component comprising an anode and a cathode arranged oppositely, and a functional layer arranged between the anode and the cathode; characterized in that the functional layer comprises an organic compound according to any one of claims 1 to 13.
15. The electronic component of claim 14, wherein the electronic component is an organic electroluminescent device, the functional layer comprises an organic light-emitting layer, and the organic light-emitting layer comprises the organic compound.
16. An electronic device comprising the electronic component of claim 14 or 15.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310073444.7A CN117384141A (en) | 2023-01-17 | 2023-01-17 | Organic compound, and electronic component and electronic device including the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310073444.7A CN117384141A (en) | 2023-01-17 | 2023-01-17 | Organic compound, and electronic component and electronic device including the same |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117384141A true CN117384141A (en) | 2024-01-12 |
Family
ID=89439782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202310073444.7A Pending CN117384141A (en) | 2023-01-17 | 2023-01-17 | Organic compound, and electronic component and electronic device including the same |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117384141A (en) |
-
2023
- 2023-01-17 CN CN202310073444.7A patent/CN117384141A/en active Pending
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN114133332B (en) | Organic compound, electronic component, and electronic device | |
| CN113651826B (en) | Nitrogen-containing compound, and electronic element and electronic device using same | |
| CN114456174B (en) | Nitrogen-containing compound, and electronic component and electronic device comprising same | |
| CN114133333B (en) | Nitrogen-containing compound, electronic component and electronic device | |
| CN115960001B (en) | Organic compound, and electronic component and electronic device including the same | |
| CN115385898B (en) | Nitrogen-containing compound, organic electroluminescent device and electronic device | |
| CN115650899B (en) | Nitrogen-containing compound, electronic component and electronic device | |
| CN114335399B (en) | Organic electroluminescent device and electronic device including the same | |
| CN114933571B (en) | Organic compound, electronic component, and electronic device | |
| CN113896720B (en) | Organic compound, electronic component, and electronic device | |
| CN114133351B (en) | Nitrogen-containing compound, and electronic component and electronic device comprising same | |
| CN115521214B (en) | Organic compound, and electronic component and electronic device including the same | |
| CN114230472B (en) | Organic compound, electronic component and electronic device comprising the same | |
| CN114181166B (en) | Organic compound, and electronic component and electronic device including the same | |
| CN117384141A (en) | Organic compound, and electronic component and electronic device including the same | |
| CN114989179B (en) | Organic compound, organic electroluminescent device using the same, and electronic device | |
| CN114075166B (en) | Organic compound, and electronic element and electronic device using same | |
| CN114426539B (en) | Organic compound, organic electroluminescent device and electronic device comprising the same | |
| CN115490569B (en) | Organic compound, organic electroluminescent device and electronic apparatus | |
| CN114497424B (en) | Organic electroluminescent device and electronic device including the same | |
| CN113666832B (en) | Organic compound, and electronic element and electronic device using same | |
| CN116143703A (en) | Organic compound, and electronic component and electronic device including the same | |
| CN117551110A (en) | Organic compound, and electronic component and electronic device using same | |
| CN117384047A (en) | Organic compound, organic electroluminescent device and electronic device comprising the same | |
| CN116332826A (en) | Organic compound, and electronic component and electronic device including the same |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination |